


First Encounter

by inkstainedcas



Category: Supernatural
Genre: Awkward Sex, Dean and Cas are 18, Dean's just a sweet idiot, Destiel - Freeform, First Time, High School AU, M/M, Teen AU, clueless, just leading up to it, not really slash
Language: English
Status: Completed
Published: 2018-05-25
Updated: 2018-05-25
Packaged: 2019-05-13 18:17:31
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,834
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14753867
Author URL: https://archiveofourown.org/users/inkstainedcas/pseuds/inkstainedcas
Summary: "People didn’t always have Google to tell them how to lube their boyfriend up, Dean.”“Well, maybe they should’ve.”Or: The one where Dean and Cas are trying to figure out exactly how this sex thing works.





	First Encounter

“I feel like I’m gonna fuckin’ break you or something.”

On the bed, Castiel groaned in annoyance and rolled over, laying on his back as he stared up at his boyfriend. “You’re not going to _break me._ You have a severely overinflated idea of the size of your dick, Dean.”

“Do not!” Dean huffed, rolling his eyes right back at Castiel. “It’s just so, like. Small.”

“What is?”

“Your ass.”

Cas twisted a little and glanced down with a light shrug of his shoulders. “I thought you liked my ass.”

“No, not your _ass_ ass, I meant your, y’know.” Dean rubbed at the back of his neck and sighed, dropping onto the bed next to Cas. “Where it goes in.”

“If you can’t talk about my asshole, then maybe you shouldn’t be putting your penis in it,” Cas pointed out with a knowing raise of his brow. “Look, we talked about this. People do it all the time. If it was breaking people, I think we’d have heard about it by now. Girls do it, too.”

“Yeah, but aren’t girls, like. Built for that?” Dean asked, genuine confusion on his face.

“God, Dean. Remind me again of all the women you’ve slept with so I can formally inform them that you think their assholes are specifically built for anal sex.”

Dean pulled a face and dropped onto his back as well, his head rolling to the side so he could better look at Castiel. “Sounds gross when you say it like that.”

Cas furrowed his brow, a slight crease appearing just above the bridge of his nose as he did so. “Anal?”

“Yeah. Sounds germy.”

“You’re an idiot. Maybe I should just give you another blowjob. Or you could give me one,” Cas pointed out leisurely, his bare legs hanging off the end of Dean’s mattress. “This seems like a lot of work just to get off.”

“No, wait,” Dean protested quickly, “we can do this. Just…Google it again.”

“I am not spending all night Googling how you’re supposed to fuck me. That’s the least sexy thing I can imagine right now.”

The green-eyed boy shrugged with as much innocence as he could muster at the moment and reached out, fingers automatically tracing the subtle dips and planes of Castiel’s chest. “Then maybe we should just go for it and see what happens.”

“You don’t sound very confident in that.” Cas rolled onto his side so he could see Dean better and slung his arm across the other’s waist so he could trace circles on his far hip. God, how he loved Dean’s hips. Football and puberty had been so good to him and the prominent V Cas could spot at Dean’s waistline was enough to make him want to crawl right on top of his boyfriend. “Maybe you should try, first.”

“Me?” Dean sputtered, clearly caught off guard. “But I’m-“

“You’re what, Dean? The man’s man here? Please, you’re the one I caught looking at toys the other day.”

“There was a good sale,” the Winchester pouted. He reached out and threaded his fingers in Cas’s hair so he could more easily pull him in for a kiss. When it broke, he sighed under his breath. “I dunno, Cas. Porn makes it look so easy.”

“Based on what I’ve gathered, porn skips the several minutes of you trying to get me stretched out enough to fit it in without tearing anything.”

Dean’s eyes opened so wide it was almost comical. “But you said—”

“I said you wouldn’t break me, not that it would be a good idea to shove it in me without prepping me first. Maybe you really should go first. At least I know to be careful,” Cas snorted. Lazily, he clambered up on top of Dean and leaned down to kiss him back, a little harder this time. “Come on, De. We have your house to ourselves for hours and I want you. Don’t get cold feet now.” There was a moment’s hesitation, but before long Cas had decided to tease his boyfriend and _accidentally_ dropped his hips down so Dean’s dick nudged against his ass. “I’d be so disappointed, baby.”

Dean let out a soft moan at the friction, though he frowned dramatically at the pet name that left Cas’s lips. “Baby’s my car,” he pointed out matter-of-factly. “I ain’t your baby.”

Stubbornly, Cas shook his head. “Sure, you are. It was mostly a joke, but now it’s decided. My sweet, handsome, blissfully ignorant baby who told me this morning that he wanted to fuck me into next week and can’t even get it in me now.”

“I take offense to that. Maybe I just have a really big dick,” Dean insisted pridefully. “You ever think of that?”

“I know what a dick looks like, sweetheart. I promise yours isn’t bigger than that of any other man who wanted to sleep with his boyfriend. Plus, we’re pretty much the same size, so calm your ego for a second, would you?”

Dean paused, taking a long moment to think about it. “Mm, maybe we both have really big dicks.”

“If you say so, handsome.” Cas rolled his eyes, though fondly, and dipped his head down to kiss at Dean’s jawline in hopes of drawing a reaction from his sensitive boyfriend. He loved when Dean’s hips rocked up for him, loved when little whines escaped between barks of the other’s deep voice. Loved _Dean_ , actually, which may have been the only reason he was so willing to sit there and analyze every detail with his paranoid partner.

Sure enough, Dean moaned a little, his hips jutting up just enough for him to catch a little more friction from the body above him. Castiel smirked against Dean’s skin and nipped at the sweet spot he’d discovered at his neck, biting down before soothing it with a kiss. Satisfied that he’d left a small mark, Cas pushed himself back up by supporting himself with his elbows and grinned down at Dean. “There. Now you’re all mine, so let’s get this moving, because your mom won’t be out forever, and the last thing I want is your family coming home in the middle of you fucking me.”

“Dude, Cas, don’t talk about my mom when I’m trying to have sex with you. It’s a boner killer.”

Cas snorted a little and moved up just enough to give Dean a proper kiss, instead. “Sorry, baby. Won’t happen again.”

Dean had long since given up on fighting the nickname, at that point. Once Castiel was set on something, that was that. And maybe Dean didn’t mind quite as much as he led on, anyway, which he guessed Cas probably knew even better than himself.

Dean was quiet for a moment, his hands finding purchase on Cas’s hips as he looked up at the other in thought. “Maybe if we find some of the like, really boring homemade porn, it’ll be more realistic.”

“You want us to sit in your bed and watch porn on your phone until you figure out how to have sex with me?” Cas asked, amused and incredulous. “Come on, Dean. We already went to the store and had the most uncomfortable encounter with the girl from our chem class last year behind the register. If that lube goes unused tonight, I might cry.”

“Crying isn’t sexy, either,” Dean pointed out, a smirk playing at his lips.

Cas shrugged. “I’m sure someone’s into it. I don’t know. Maybe we should just…bite the bullet. If something’s not working, we’ll figure it out. People didn’t always have Google to tell them how to lube their boyfriend up, Dean.”

“Well, maybe they should’ve.”

A laugh escaped Cas’s lips and he pecked Dean’s cheek. “I’ll be sure to go back in time and pass along the message. Ask why the hell they waited so long to invent Google. I’ll have to get back to you on that, though. I have plans tonight.”

“Plans?” Dean parroted, looking genuinely concerned. Castiel gave it a few moments, barely able to restrain from rolling his eyes, before it seemed to click in Dean’s mind. “Oh. You meant with me.”

“Yes, I meant with you, you beautiful idiot.” Cas pushed himself up and reached over Dean and across the bed to grab his phone and check the time. “We’ve already wasted a half hour trying to figure this out. I’m telling you, just do something to me and I’ll be louder than ever since we’re in an empty house and stroke your ego for you. Worst case scenario is you get a confidence boost and a blowjob as a condolence prize.”

“You are getting good at those,” Dean hummed with a serious nod. “Next time it’s your turn, promise. I just…damn. I like when you do it.”

“I’m not sure there’s a ‘one boyfriend gets off per night’ rule, you know. We could _both_ do it next time.”

“You mean, like…” Dean made a gesture, vague and pretty much useless, but Cas knew his boyfriend well enough to see what he was getting at.

“No, I wasn’t talking about a sixty-nine, babe. I haven’t even thought about that since people beat the joke to death back in middle school. I just meant taking turns.”

Dean pouted a little at that, not bothering to hide it. “Got me excited for a minute there, Cas.”

Cas arched an eyebrow at Dean and let out a soft laugh. “Seriously? That’s what you want?”

Dean floundered at that, searching for an easy defense, but Cas was already rolling his eyes and dropping another kiss to Dean’s lips. “Maybe another night, babe. Now,” he tacked on, his voice firm as he reached out to drop his phone onto Dean’s end table. He grabbed the small bottle that was sitting there instead and all but shoved it into Dean’s hands. “Are you going to fuck me, or are we going to lay here and watch Dr. Sexy all night?”

“That might get me in the moo-“ Dean started, a cheeky grin flashing over his face, though he quickly faltered at the look Cas shot him. “Sorry, sorry. You’re so much hotter, et cetera, et cetera. It’s just, y’know. He’s _Dr. Sexy._ ”

“And you’re ridiculous,” Cas pointed out matter-of-factly. He adjusted himself and settled back in, giving a lazy grind of his hips against Dean’s. He pretended to ignore the _whimper_ that escaped his boyfriend’s mouth as he did. “We only have one more hour, Dean. I swear to god I’ll leave you hanging right on the edge if your family comes home in the middle of us having sex because you put it off for so long.”

Dean’s pout had to be award-winning. “Fine. But, and I’m just sayin’, if my dick’s too big for you…”

Cas groaned and claimed Dean’s mouth again, this time more deeply, if only to stop him from finishing his sentence.

“ _Stop talking about your dick and use it, Winchester.”_

**Author's Note:**

> I'm considering starting a series of drabbles/short stories in which Dean and Cas are lovestruck idiots during sex, possibly based off of this tumblr post:https://beef-jerk-me.tumblr.com/post/173899423133/i-am-sick-of-the-same-old-smut-in-fanfics
> 
> Who's interested? Let me know here or at my tumblr! inkstainedcas.tumblr.com


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